For The First Time
by robert3A-SN
Summary: Jeff and Annie have been together for three months, yet Annie hasn't let Jeff go all the way with her, for reasons Jeff is unable to get out of her until now. Rated M for smut in chap 2; based on a Milady/Milord fic prompt.
1. Chapter 1

**Based on a Milady/Milord Ficcy Friday prompt from butterbadger**

It was happening again. As per usual, Annie was finding ways to get out of sex. And this one wasn't even original.

Once Jeff started to get his hands under Annie's shirt, she looked at her watch, called out "Look at the time!" and explained that she needed to go home and sleep. She claimed Troy and Abed needed her to get up early and be their script woman tomorrow – which was the same excuse she used the second time Jeff made his move. She wasn't even trying to come up with new excuses anymore.

It had been three months since Jeff admitted he wanted to be with Annie, and everything was going good since then – except this part. Every time they made out and Jeff tried to get a little more from Annie, she backed off and made up some excuses for stopping. But the excuses were getting worse, and Jeff was getting more frustrated and downright confused.

In the past, Jeff wouldn't have put up with this for more than a week. Two weeks was his previous best waiting period. But he had put up with _three months_ of having no sex with Annie – not to mention the already painful _three years _of buildup beforehand. If he was going to keep enduring this, he had to know exactly what phobia, neurotic quirk or paranoid thought he was dealing with.

"Okay, what is it?" Jeff finally asked straight out, as Annie got up from Jeff's couch and tried to straighten herself up. "What phobia, neurotic quirk or paranoid thought are we dealing with here?"

"Huh?" was all Annie could get out. "I, um, don't know what you're talking about, Jeff. And I have script woman duties to think about anyway." Yeah, that told Jeff he was _way _off base to suspect something.

"Come on, what's the problem? Are you still too hung up about….._sex_?" Jeff asked in an Annie-like whisper to try and lighten the mood. But Annie just gasped like usual instead of laughing, so maybe he wasn't entirely on the right track. So he got more reassuring by saying, "I think I've seen enough role playing games, Christmas songs and paintball wars to know you're on the right track."

"_Jeff_! That has nothing to do with anything," Annie stammered out.

"Okay then, that rules one theory out," Jeff crossed out. "So if it's not that you don't know what you're doing….then I know too much, then?" he guessed, then actually smiled a bit when Annie didn't answer. "I see. Well, luckily I've had that effect on a lot of – people," he stopped before he started bragging about his past conquests, at a worse time than usual. "But that means I know how to get around that, you'll be fine!"

"Jeff, you don't have to push this," Annie insisted more firmly.

"Annie, I'm pushing this for _you_," Jeff reminded. "You've been too nervous to even sleep with me since we got together. If there's some serious hang-up you have, I want to help you get past it. And not _just _to snap the longest drought of my sex career! I mean, we're in a relationship now, and I pretty much have to-"

"I know this isn't real, Jeff!" Annie blurted out. Why the hell she did was another very confusing matter. Jeff certainly couldn't think of anything for a good 10 seconds.

"Annie….have you been getting funny dreams from watching 'Inception' again?" Jeff inquired. He thought Abed agreed not to play that movie while she was in the apartment anymore. But it appeared Jeff had to alter the plumbing for Abed's mini-Dreamatorium 2.0 after all.

"No, Jeff, I know we're not in a dream within a dream within a dream this time. And I only had that nightmare and believed it for _one _morning, okay?" Annie clarified. "Okay, maybe real wasn't the right word after all. What I meant was….I know this isn't a regular, serious relationship. So you don't have to pretend it is."

Jeff had no idea how it got to _that _topic of conversation. So it was probably best to clear up his old questions first, before he took on these new weird ones. "What does _anything _about that have to do with not wanting to sleep with me?" he tried to ask with a level head.

"I'm going to get to that," Annie promised as she seemed a little nervous now. This was pretty damn fitting at this point of the conversation/budding argument.

"So get to it, if it's not too much trouble," Jeff pressed, unable to contain_ all _his rising snark/annoyance. But he tried to keep it in check while Annie was explaining herself.

"Jeff, I'm not getting carried away about what this is. I did assume things about what we could be once, but I can't do that anymore. We're not some fairy tale romance, and that's all right with me now. So I'm just taking this for what it is before it ends someday," Annie stated, although she wasn't exactly clearing things up yet.

"And what _exactly _is this?" Jeff asked. "I remember saying a few months ago that I wanted a relationship with you. Unless one of us heard me wrong, I don't see the confusion here."

"But you're not a relationship kind of guy, Jeff. It took me a while, but I got the message," Annie assured. "I don't have some romantic dream that you'd change your lifestyle, change your thoughts about couples and marriages, and stop telling people to nut up and die alone. " Jeff nearly chuckled at Annie using the word "nut" in a dirty context without blushing, yet he was still too confused and annoyed at her.

"You have relationships once in a while, like this one. But you don't believe in settling down and committing for the long haul. And if I tried to change that, this whole thing would be ruined and we wouldn't even be friends anymore. So I'm not going to," Annie promised, as it started to dawn on Jeff where she was going with at least 10 percent of this.

"This is just a casual relationship that'll probably end before we graduate and go back to the real world. Since I know that, I can let myself have fun until you end it, or we end it together, and we can still be friends later. That's sure better than the alternative," Annie figured.

Jeff couldn't figure that much, yet in his struggle, he remembered a still unanswered question. "So you won't have sex with me unless we're in a real long-term relationship? Annie, even for your new devious side, that's a low blow. And I'm less inclined to mean that in the dirty way now!"

"No, no, that's not it!" Annie cried out. "I'm afraid to have sex because it'll make me forget everything I just said! I'm afraid it'll make it harder for me to lose you later! And there's nothing dirty _at all _in that, Jeff!"

There may not have been anything dirty, but the odd, sad and somewhat insulting stuff was still there to make up for it. "You mind going a little deeper into that?" Jeff said, not even bothering to clarify his proper context for the word "deeper."

"Jeff, I know how to have sex with you by now. I know it would be incredible, and you'd go all out to drive me crazy. But it might be _too _incredible. You'd be the first man to ever show me how great sex can be, and that might make me _too _happy. So much that I forget it won't last forever. At least until it actually ends," Annie predicted.

"Well, if that's the case, fine! 50 percent of the Winger touch is still better than 100% from everyone else! I can go down to 40 percent, but that's as much phoning in for sex that I'm comfortable with," Jeff offered.

"Jeff, that's not helping!" Annie insisted. "I already know that's the one thing you _really _put an effort in! If I let you do that….it'll just hurt more later."

"And later is what again? When I dump you, like I haven't done yet except in your mind? Do I have that right?" a more annoyed Jeff countered.

"I know you're not going to dump me yet!" Annie shared. "I figure it'll happen after graduation, or after we try and fail to make it work a few extra months. Either way, once it gets real, I know that'll be it. And once we have sex, it'll _start _getting real. Then it'll be all downhill from there. I mean, by then, what's left for us to really do?"

"So you think I'll just have my way with you, then get bored and dump you?" Jeff tried to understand – then moved onto getting angrier. "You actually think I would do that to you?"

"Oh come on, you bragged about doing that to women all the time!" Annie reminded.

"That was other women, you're _you!_" Jeff stated, although holding Annie up on a pedestal even while yelling at her was a steep contradiction. "Why do you think I'd be that awful to you?"

"It wouldn't be the first time. I mean, you'd be having sex this time instead of kissing me before summer. And you probably wouldn't stay away from me for the next three months this time," Annie finished comparing. "But after dating me, kissing me, having sex with me, seeing me naked….there isn't much more you could do before you got scared off. I thought the longer I put off the sex, the longer we could enjoy ourselves before we tanked afterwards."

"And we're back to you being _so _convinced we'd tank," Jeff attacked, if only to do _something _other than forget that summer. "So you thought withholding sex forever would stop that?"

"No, Jeff, I _was _going to do it, I promise! Just after a little while longer, that's all!" Annie promised. "Just until I had a bit more fun doing other stuff with you. Then once we finally had sex, I could live with things falling apart from there. And contain the damage to save our friendship."

"Funny how _I'm _the only one doing the damage in this fantasy of yours, isn't it?" Jeff cut in.

"Oh, I know it won't be all _your _fault! But I'm sure I'll do something to make you afraid at some point, whether I mean to or not!" Annie predicted. "Jeff, I'm not attacking you for it! I understand you don't want to be with someone for a long time! I didn't let myself understand it before, but I'm not that naïve schoolgirl anymore! I just want to stretch this out as much as I can before we've both had enough."

"Sounds like _you're _the only one that's had enough here," Jeff shot back. "You know, I _have _jumped through a lot of hoops to get out of relationships. But _you're _shattering my world record and then some here!"

"Why are you mad at _me? _I'm giving you an out for the future!" Annie reminded. "You don't want the trouble of something real, and I'm trying to spare you!"

"Maybe I don't want to be spared the trouble," Jeff admitted before he caught himself. But soon enough, he realized he'd have to elaborate.

As awkward and somewhat lame as the rest of this would make him, he felt like he had to go on. After being told over and over that he would feel scared or smothered by Annie, it was time to get some facts into this.

"Maybe I _want _the trouble," Jeff stunned Annie by saying. "I haven't wanted the trouble in just about _ever_. But with you, it doesn't seem so….troubling."

"Jeff, you don't have to spare my feelings here," Annie disclosed. "I don't want to nag, guilt or manipulate you into saying something you don't mean. Or to do something you don't really want to do. Or think you want to say or do now, but regret later. I'm not that kind of person anymore, you can be fully honest with me."

"I _am_ being honest," Jeff laid out there, without letting himself do any second guessing.

"Come on, Jeff, you're the most anti-commitment person in this state!" Annie low-balled. "And you've only officially dated me for three months! Why would you _mean _that you actually wanted a real future with me?"

"Because I love you, okay?"

Now that _really _got away from Jeff.

Yet within three seconds, he realized he really regretted it not because of what he said – but because he didn't want to say it like _that_. Certainly not during an argument.

He had seven more seconds to take that realization in before Annie spoke up. "_That_….is a low blow, Jeff. You don't have to say that to win this argument."

Now it was back to being mad again. More mad than ever after that, actually. "You think I said that to beat you? Annie, I've never said that to a woman in my _life!_ Even the ones I've _seen _naked! Do you think I'd say it _now _if I didn't mean it? This is real Jeff you're talking to, not the evil fantasy Jeff you've turned me into!"

This did manage to take Annie back a bit. Yet she tried to recover by saying, "Jeff, I'm not trying to make you evil. _You've _said for years that love and relationships and couples and being with someone is a waste of time. I didn't believe you meant it then because I was naïve! Now I finally believe you! Didn't _you _want me to be more grownup and not so oblivious anymore?"

"Not like that, I didn't. I wanted you to be grown up _and _still believe in that stuff. I didn't know I killed that part of you _that _much…." As his familiar Annie guilt started kicking in, Jeff willed himself not to dwell on it until the argument was over. With that, he got back into defensive, offended mode.

"Second of all, you're basing all this on the _old _Jeff! Jeff since three months ago is different now! He does couples stuff now and he _likes _it! He goes on dates, doesn't _need _sex all the time and actually treats his girlfriend like a princess! But that's not enough for you, is it?" Jeff accused.

"Well, um…." Annie regrouped. "Well, how am I supposed to know that? That just proves you're good at taking me out! You're no good at that in the long term, you've made that clear for years!"

"That doesn't mean I don't want to try! And I've never wanted to _try _with anyone until you!" Jeff pointed out.

"How am I supposed to know that for real?" Annie countered, halfway proud that she wasn't thrown off her argument – while her heart still halfway fluttered in her chest. Yet she didn't want that to get the best of her, so she pressed on. "You don't have the best record on being clear with me! Believing in some romantic you has hurt me too much already! And you still never _apologized _for doing that _so many times,_ either! So forgive me if I'm a little skeptical, Jeff!"

Jeff just stayed quiet for several moments, then responded quietly. "You don't believe in me. You don't think I _can _change. You still think the sooner I have sex with someone, the sooner I'll lose interest and end things when they get real. That was the _old_ me….but I haven't done any of that in a _long _time, Annie. But you're judging me for who I was _then_, not for who I'm trying to be _now_!"

Now Jeff was in full on righteous anger mode, although he wasn't full on out of control as he continued. "You're the _one _person who always believed I could do anything. That's the biggest reason why I'm even _close _to being a good boyfriend now! But if you're still convinced I'll relapse, how do you think _that _makes me feel? I want _everything _with you, Annie, or at least I want to want it! But how am I going to do that if _you _don't believe I can? Or if you're trying to tell yourself you don't?"

Jeff just wanted this to be over with, before he said something he would truly regret – or before he made Annie so upset that this dragged on all night. She just looked stunned and taken aback, so he figured he had room for one more closing remark. "I expect to be judged like that by Britta, or Pierce, or even Shirley. But _you_….if _you _don't even have faith in me, then…."

There was no way to continue that thought without being really hurtful. So in another example of how Jeff really _was _changing, he just stopped there and headed to bed. He shut the bedroom door, trusting that Annie would show herself out and let them both cool off until tomorrow.

Jeff didn't hear anything, so he figured he could go to sleep and shut this out for a while. He changed into his perfectly ironed bed clothes and made sure not to get a wrinkle on them when he laid down. He then tried to go to sleep, but it wasn't really working.

He still thought about how Annie didn't believe he could be a serious boyfriend, or didn't want to believe it. Then again, he really gave her no reason to think he would be before now. But he thought acting like a real, committed boyfriend for three months would have told her different already!

Then again, Annie wanted actions _and _words, without any wiggle room to doubt them. And three _years _of doing the opposite for her couldn't quite balance out three_ months_.

At that distressing thought, Jeff heard the door to his bedroom open. He knew who it was, but kept his eyes closed, in case Annie came to yell or do some other troubling thing. He stayed still and kept his back turned to the left, yet almost opened his eyes when he felt Annie sit behind him on the bed. He did finally open his eyes when he heard her lie down, then saw her right arm reach over his waist and come into his view.

Jeff saw Annie's hand tentatively search for one of his, yet could tell how hesitant and nervous it was – or rather, she was. It must have said something that he could read Annie's thoughts, nerves and regret just how looking at her hand.

But he took mercy and let his right hand gently touch hers, then let it slowly slip into his. Her thumb still glided slowly and uneasily over his skin, yet Jeff let her get comfortable and reassured before she finally relaxed.

"I'm so sorry, Jeff," he heard Annie say while lying behind him. "I….I just didn't want to get carried away like a child again. But I guess I went the other way. This time I really _did _see things in you that weren't there, huh?"

"No. You didn't," Jeff admitted. "I did make a good case for you to think that way. And I'm sorry for that….and all the other stuff. I _always_ have been."

"I know. Or I liked to think that I knew," Annie voiced behind him. "Now I know for sure, so thank you."

"Well, here's more stuff you should know. Just so we're completely on track now," Jeff started. "A lot of me _does _still think real relationships are lame. But I don't want to believe that'd be true with you. I thought I was making that clear before, but just in case…."

Jeff swiped his thumb over Annie's hand and focused on it, as he willed himself to get into sappy mode. "I want to want a real future with you, Annie. I mean, we've dated for three months, but I've had some form of deep feelings for you for just under three years. And I've admitted it to myself for about a year. That's long enough to know I want that long term stuff with you. I'm just not sure I can _give _it to you, even if I try. And if you don't believe I can do that anymore, how can _I_?"

"Jeff, I do believe it, I do! I've _always _believed in you! With a few glaring exceptions, obviously. I just….I just wanted to make sure I'd be okay in case you couldn't. And that _we _could still be okay too," Annie explained.

"Well, maybe now I can help you be okay in other ways," Jeff offered. Annie didn't say anything, but when he felt her kiss the back of his neck, that seemed to be an answer.

"I think that's better than the alternative," Annie concluded. "I really _am_ so sorry, Jeff."

"Annie, it's good. We're good," Jeff assured, trying not to sound dismissive. He rubbed her hand again to calm her further, promising, "Now that we're on the same page for the first time in three-and-a-half years, I think we're going to be fine."

"Finally," Annie exclaimed, which made Jeff chuckle for reasons he didn't entirely get.

Jeff didn't turn around to face Annie, or kiss or try anything else with her although they'd made up. He just settled for holding her hand, stroking it, and batting their fingers together playfully for no real reason at all. This actually entertained them both and soothed them as they drifted off, with Annie snuggled against Jeff's back and her arm draped around him.

It was almost hard for them to remember that this started because of sex, since it led into much deeper issues. Yet the end result still came full circle.

For the very first time, Annie Edison actually slept with Jeff Winger that night – even if they didn't "sleep together." And for the very first time, Jeff actually slept with a woman without making a move on her, and without any intention of having sex that night or afterwards.

Combined with how Jeff said "I love you" – which would have to be fully addressed another time – this was a milestone night in ways Jeff didn't anticipate an hour ago. But he knew _just _enough about being a good boyfriend to know that wasn't a bad thing. Not at all.

With that, any other milestones on the backburner could take their time now.

**A/N 2: Jeff's "trouble" lines are mostly taken from "How I Met Your Mother"'s fourth season finale, when that show's own womanizer in great suits made a love confession.**


	2. Chapter 2

Annie felt a big lump next to her when she woke up. At first, she briefly thought Abed was filming Troy in a death bed scene in her bed – while she was in it – without permission again. But when she actually opened her eyes, she got clued in.

In a flash, she remembered who was in this bed, whose bed this really was, and what happened last night to get them there. When it registered that she slept in the same bed with Jeff Winger for the first time, her heart did a little cheer. When it remembered how it happened, it turned in its pom-poms.

And here Annie had thought she was really becoming a grownup. That by treating things with Jeff so casually and taking his anti-commitment speeches seriously, she was being smart. That she could enjoy being in a relationship with him and be protected when Jeff inevitably ended it. That sex would either make it too serious, or scare one of them off. And that Jeff only wanted to cross Annie off his Greendale bucket list, and would lose interest after getting _everything _from her.

God, Annie really was a Britta. Her and Jeff assumed the worst in people, even when all evidence was to the contrary – not Annie.

But she had assumed a worst part of Jeff that wasn't there anymore, or at least wasn't in control of him like before. Yet after years of heartbreak and setbacks, Annie wanted to be prepared to get let down – even after Jeff started dating her. Even after she should have known she wasn't dealing with _that _hurtful, distant Jeff anymore.

The one who never said he loved Annie.

God, she even ruined _that _milestone too. And after groaning, she noticed that she could add waking Jeff up to the list of screw-ups. Though his back was still turned from her, like last night, he stirred and managed to turn himself around to face her.

"So was it good for you?" Jeff quipped, which made Annie blush a bit and nearly whisper that they didn't have sex. Yet as Jeff smirked, Annie figured that was just what he wanted, so she bit her tongue and stopped blushing.

"It could have been better," Annie tried to joke, but this reminded her how last night really could have been better. She already apologized to Jeff enough in bed last night, yet a few more sorry's might be needed. "Jeff, even if you don't want to keep hearing it, I'm still really sorry," she started.

"Kind of early to beg for forgiveness I already gave you, isn't it?" Jeff wondered. However, this inspired Annie to come up with another tactic.

"Then I'll go with the thank you's instead," Annie offered. "The thank you's I should have given you for being such a good boyfriend. You really have treated me like a princess and I am _so _proud of you. I just thought if I focused on that, it'd be too hard if…..or _when_, like I figured….you had enough." She stopped that line before going into apology mode again.

"I wanted to treat this stuff like I thought a grown-up would. Practical and realistic and not with my head in the clouds. You hated that anyway, and I wanted to make this easy for you while I could. Of course, the one time I believe that _you _believe your cynical nonsense about relationships, I get it wrong. What do you know?" Annie reflected.

"Well, it's not like I helped you know better," Jeff admitted.

"But you have in these last few months! I believe it now, and I'll never doubt your commitment again! Not until you give me an actual _reason _to!" Annie promised.

"I admit I might give you a few," Jeff said, which took Annie aback, just when she thought they were on a sentimental roll. "Annie, you are right. I might always believe that relationships and love are stupid. Even if I know you're the exception that proves the rule. I don't want to be too lame and sappy to be my usual awesome self – but I don't want to be too awesome to be a bad boyfriend to you. I want to be _both! _The cool, awesome winner the world knows me as, and the….better version I am with you."

"Aw, Jeff," Annie choked up. "Well, those two Jeffs_ are_ pretty spectacular together," she conceded.

"So are yours. Your two Annie's, I mean," Jeff started again. "I get that you weren't being naïve and you were being practical. I love that you're doing that. But I love the old Annie more, no matter how I tried to deny it earlier," he let out. "I want you to be the same sunny, bubbly, pain in the neck we all wind up loving to death anyway. Combine that with the grownup Annie, and you two will rule the world in days!"

"Jeff, I should probably graduate first before I rule anything. And technically, I want to be _elected _to the job, anyway," Annie stated, surprised but pleased that she actually teased him back instead of melting into goo. The grownup Annie really was alive and well, and being used for good this time.

"Of course you do, your Highness," Jeff promoted her up from Milady. "But I think voters want to see you be the kickass Annie you've turned into, and the kickass Annie you've always been. Keep those two sides together, and no smear campaign or dumbass co-worker can stop you."

"I will if you will," Annie proposed. And despite the labored metaphor, the basic point was true.

If Annie could combine her new skepticism and growth with her usual optimism and big heart – and not favor one side over the other – the results may well be epic. They certainly were when the new caring Jeff and the old awesome Jeff came together to iron out their rough edges.

And the way both their new and old sides came together reminded Annie so much of how her and Jeff did. Alone they were formidable, but together they might be unstoppable. And now that Annie could feel safe to think like that again, she was almost at a loss for words. So she used her kisses instead.

In the middle of their soft, slow making out, some words did finally pop up in Annie's mind. "You love me," she remembered as she nuzzled into Jeff's neck.

"Who gave it away?" she heard Jeff inquire, feeling the rumblings of laughter in the hard chest pressed against her.

"Oh, just some jerk," Annie mumbled, making sure to suckle on Jeff's neck extra sweetly so she could have the last word. As Jeff groaned from it, Annie suddenly wanted to hear him make that noise for her again. And again.

Once he did two more times, she wanted more – and without thinking about what that meant, she reached down to the bottom of Jeff's shirt. Yet after her fingers brushed Jeff's belt, Jeff inhaled sharper than Annie had ever heard him, then stopped her from going further.

"Annie, are you….?" Jeff couldn't even finish asking. But Annie didn't need him to, as she just nodded yes. "Wait a minute, this means our….first time would technically be makeup sex! Is _that_ how you want it?" he made sure.

"Well, knowing you and knowing me, we'll probably need a _lot _of makeup sex sometimes. Might as well start practicing now," Annie reasoned. And with that acknowledgment that there might be a future in this after all, she rolled on top of Jeff and resumed suckling on his neck even more passionately.

However, Annie was in no hurry – although she really did have to get going and help Troy and Abed soon. Yet that was the furthest thing from her mind, as she started enacting the fantasies she struggled not to indulge in for three months. She broke from Jeff's neck and tried to get his shirt off, but Jeff soon took care of it for her. With that, Annie got her own shirt off herself, then laid back on top of Jeff with only a bra covering her top half.

She then went back to a slow, sweet treatment. Now that she could finally let herself kiss every inch of Jeff Winger, and that Jeff wanted her to, she wanted to fit in as much as she could. Annie put her left hand on Jeff's waist and her right on the back of his head, and kept the rest of her body below the neck still as her lips and tongue did the real work.

They kissed and nibbled up to his left ear, then kissed back down across his neck and all the way up to the right ear. Her right hand gently played with Jeff's precious hair as the left started to glide up to his brilliant abs. Meanwhile, her mouth went across his cheek and then gave him a few brief, fleeting kisses with tongue before returning downwards to his throat.

Annie was so focused on kissing as much as possible that she almost tuned out Jeff's moaning and groaning. Yet she couldn't tune out how his hips rose up and collided with her centre after that kiss – and the obvious things she could feel from it.

Jeff was raging hard and Annie hadn't really done anything. She didn't even get to the steamy stuff and ideas she kept in the back of her head. All she was doing was the sweet, romantic, gentle stuff to get that of the way before going hot and heavy. And yet as she examined Jeff closely, he looked close to the brink just from the gentle kisses and caresses. That was….somewhat surprising.

No matter how much she wrongly assumed about Jeff, Annie _knew_ he didn't do this kind of sex too often. He was an overwhelming force of nature in bed, at least according to his biased opinion, and likely didn't have the time or motivation to be romantic with sex.

But in this case, it only took slow, gentle kisses and rubs to drive Jeff crazy. She couldn't even blame his erection on morning wood, since they talked long enough beforehand for it to go away – probably.

If not, then the conclusion was that this kind of sex did turn Jeff on. Or at the least, it turned him on when it was done by Annie. It couldn't just be because it'd been a while without sex for him – likely longer than most times for him. If he was that built up, he would have devoured her right away, but instead he let himself get swept away like this. Like he likely hadn't by any other woman before.

Yet once again, Annie was the special exception for him that no one else had been. And now that she'd thrilled Jeff in a new way, she wanted to thrill him in old ways like no one ever had before.

But just as Annie moved down to kiss his chest more intensely, and was about to head for his nipples and abs, Jeff chose then to suddenly leap out and put her on her back. "Jeff! I wasn't done yet!" Annie called out.

"Yeah, but _I _didn't want to be done yet," Jeff gasped out. "You've done enough making up for last night. I have three years to start making up for, thank you."

To begin that quest, Jeff started devouring Annie's neck and hit her most sensitive point right away. Annie now began to gasp, especially when Jeff's arms went underneath her and wrapped around her, pressing her half naked body right up against Jeff's. He then grinded a bit against her, which set Annie off on another series of moans and made her hug him close to her as well.

Jeff set off a few more goose bumps by trailing his hands down Annie's waist and then grasping the top of her skirt. His mouth soon trailed down to the top of her chest while slipping her skirt down until her panties were exposed. Once they were, his hands slowly went up the top of her legs and grasped her panties next, pulling them down just low enough to expose Annie's crotch.

Finally Annie tried to get her skirt and panties completely off herself, but Jeff got off her briefly and took care of that. This left him the perfect angle to look down at how Annie was nearly naked except for her bra.

"I waited all this time for that…." Jeff all but whispered. Before Annie could put her brain back together, Jeff added "Worth. Every. Minute." and then put himself right back on top of her. For good measure, he grinded his still covered erection against Annie's now bare pussy and almost made her voice give out then and there – among other things that almost gave out.

"Jeff, please, touch it for real….." Annie somehow had enough strength to ask. There wasn't much more she could say, as Jeff's steamy yet still sweet tactics were making her gasp too much to talk. And that was before he started brushing his hand over her opening. And before he put his thumb above her vagina and had his other fingers glide over her outer lips without dipping in quite yet.

Then he went and started kissing her still bra-covered breasts for good measure. Although Jeff didn't take the bra off yet for some reason, he still kissed and suckled her nipples and the rest of her clothed flesh through the fabric – which was still plenty hot anyway. So were the two fingers gently making their way inside Annie, for that matter.

Jeff took one of them out and let the other go a little deeper inside. After it thrust around and made Annie arch her back – and stick her chest out further for Jeff to play with – the second finger returned inside and went in deeper as well. After a few minutes, Jeff finally took those fingers out, saw them covered with her juices, and then glided the wet fingers up Annie's stomach and towards her chest.

Annie only had a second to try and see the wet trail left on her. At that point, Jeff dove down, gave her pussy one big lick, then licked all the way up the long trail of wetness and got as much off her as he could. Now back completely on top of Annie, Jeff's tongue got right back to work on Annie's breasts and bra cups – and after seeing what that tongue did earlier, Annie almost lost it then and there.

"Jeff! Jeff, finish it, please!" Annie yelled, fighting a losing battle to keep some self control. It didn't help in that regard that Jeff put two fingers back into Annie and brushed a third against her. But right before Annie could lose it, he cruelly took his hand away and only then worked to get his pants off.

Even more cruelly, Annie only got a brief glimpse of Jeff's exposed erection before he laid back on top of her, laying his head on her neck this time. Although she couldn't see Jeff's member, she could feel it as Jeff's right hand helped rub his head against her opening now. It didn't go in, yet his left fingers returned instead – and soon he rubbed his tip against her opening as fast as his fingers were rubbing inside it.

"Jeff, God, Jeff, fuck, God!" Annie called out incoherently as she was brought to the limit. Her orgasm landed all over Jeff's left hand as his head pressed deeper into her neck. Annie's hips shook and gyrated for several seconds until she was spent, then her and Jeff barely moved as they caught their breath.

At last Jeff removed his hands and fingers from below Annie, with his left even wetter than before. Annie got a good look at her own juices all over Jeff's left fingers, which distracted her as his right hand finally pulled down her bra cups.

With her breasts fully exposed, Jeff actually rubbed her juices into her tits, then started licking them up from there. Even when he got all of her juices off, he kept suckling her breasts a few extra moments longer to be sure.

Soon even Jeff had enough with even Annie's breasts as he rolled off her. Once Annie actually unhooked the bra and threw it away, the two just stared at the ceiling for a while until Jeff managed to look at her again. "And you _really _thought…..I would lose interest in you after I did _that_?" he double checked.

"Okay, so I can be just as clueless as you sometimes, you got me," Annie somewhat hoarsely responded.

"Well, you've got a long way to catch up to me there. Probably take you 40 years or something," Jeff joked. Annie knew that wasn't a commentary on how long he expected to be in…._this_, with her. But it did remind her of how she thought this was just temporary, and would reach the beginning of the end after sex, just 10 hours ago. Yet now….

"I want to say I love you too," Annie admitted. "But after…._that, _it'd sound like a heat of the moment, post-orgasm kind of thing." Jeff smirked at her using the o-word without stumbling, which made Annie roll her eyes and smirk back before being serious again. "But we're going to finish this, then I'm going to relax, and in a few hours I'll say it with a clear head. So there's no question that I mean it."

"I think I figured out you meant it long before today," Jeff reminded her. "But you know, I technically haven't had a post-orgasm kind of thing yet." At hearing him say the o-word and seeing him point to his still hard groin, Annie finally blushed. "So does that mean I can say I love you now and you'd believe it?" Jeff proposed.

"I think you reached your quota for 'I love you's' for a while last night," Annie let him off the hook. "Don't worry, Jeff. You don't have to be sentimental _that _much if it still makes you uncomfortable. I'm willing to work with you and whatever hang-ups you still have, not attack you for them. You've earned that leeway."

"Won't saying it more make me less uncomfortable eventually? God, I already have to do all the work and sacrifices in this relationship," Jeff comically complained. Annie rolled her eyes at the last part, but then reflected on his offer in the first part and smiled more sweetly. To punctuate it, she learned up and kissed him a few more times.

"I know you love me too, Jeff. I know it _and_ I believe it now," Annie assured. "Of course, there's still one more thing you haven't done yet to prove it." Now Annie was the one to glance down at his groin, which made Jeff get the message and smirk in anticipation.

But first, Annie reached her hand down there, figuring she at least had to touch it once. Jeff backed up a bit so Annie could see her target, then she went and put it into her palm. She wrapped her hand around it and widened her eyes a bit at the feel of it, but adjusted quickly and went to place her thumb on the tip.

Annie let her thumb glide over Jeff's tip and was intrigued at how smooth it felt. Looks wise, what little she had seen from penises, or representations of them, made them look intimidating – especially for ex-prudes like Annie. Yet although this penis still looked intimidating – and as big as Annie imagined it would be – it was actually soft and firm and warm and welcoming to the touch. Kind of like its owner deep down.

Speaking of the owner, his breath seemed to be more uneven the more Annie swiped her thumb across his penis head. How very interesting. First he got extra turned on by Annie being sweet on him, and now rubbing his tip was doing a number. She had to remember these things and make sure they didn't get…..well, screwed out of her.

"Okay, I think we need to move this along now!" Jeff gasped out after two more slow thumb swipes. Annie let him get off her and reach for his desk drawer, where he got out a pack of condoms. He unwrapped one and Annie paid close attention to how he took it out, positioned it onto his cock and started rolling it over himself. This was the kind of proper condom use lesson Annie couldn't have learned or organized at the STD Fair, although this was more educational.

Annie giggled a bit at that thought and how much had happened since that infamous fair. But that spinster librarian Annie was no more, in spite of making a last stand in the past three months. Yet there would be no standing up involved here – not this time, anyway.

Jeff laid on top of Annie again, but he started off by reinserting his fingers into her. Annie clenched around them to get practice for later, as two stayed in and a third started to tease its way inside as well. Although this was still hot, she was getting a little impatient for the real thing – yet her train of thought was interrupted when the fingers pushed in her as deeply as possible.

Annie grit her teeth and closed her eyes, and thought she heard a little groan from Jeff as well. If that wasn't enough, she felt his now sheathed cock being rubbed beside her opening again. Then before she knew it, Jeff was pulling his fingers out of her – and the head of his cock then started entering her a second later.

Getting refilled like that made it go down a bit easier, although adjusting to this new size and girth was quite a task indeed. But Annie figured it probably could have been worse, if not for Jeff's finger foreplay. Of course, fingers had nothing on what was already halfway buried into her now. Then it pulled back a bit and thrust back in deeper than before, then repeated the pattern a few more times until finally sinking all the way in.

Annie rested her beet red, overwhelmed face against Jeff's shoulder, as she could feel Jeff bury his head in her neck again. Once her shallow breathing quieted down, she could hear feel even more shallow breathing against her. Interesting again….

"Worth it?" Annie forced herself to let out as a callback to all their waiting.

"Pretty close," Jeff answered, yet the fact he basically wheezed those words out said a bit more. Following a few more moments, he was able to start moving his hips back and forth again,

Annie adjusted to the movements and soon started to feel more comfortable. With the initial pain and discomfort fading away, she could let herself relax and savor this a bit more. Her hands grabbed onto Jeff's back and felt how tight and taut it was, more so than usual. Now that was something she could savor as well.

Just as she rubbed his front earlier, Annie worked on rubbing and caressing his back – and groping it after some particularly deep thrusts. Getting to feel his muscles like this, and getting to feel another big one inside her at the same time, was quite a lethal combination.

It got even better when she moved up to hold on to his arms and biceps, and had her fun feeling them up for a bit. Jeff responded by laughing just a little bit into her neck and then suckling it, so that helped too.

There was one more area left to hold onto, so Annie made her hands slide all the way down Jeff's back until they reached the target area of his ass. That cute butt stuck between those long legs and that scandalous upper body had taunted Annie for years, and now it was hers for the taking.

She grabbed onto his behind, made sure not to scratch it, and was able to use it to push Jeff deeper into her. And as she gripped his ass, pushed it forward and started to grind her hips up to his faster ones, Annie started to giggle again.

"This is fun!" Annie somewhat cheered, before a deep thrust made her groan again. She went back and forth between smiling and laughing playfully as she groped Jeff, and between groaning erotically from Jeff's own maneuvers. As she took that contrast in and saw how Jeff was gazing down at her in the process, she saw what Jeff was talking about earlier again.

The excitable little girl Annie and the wiser, experienced adult Annie were indeed coming together to make this even more fun and uplifting – to say nothing of Jeff himself.

As he leaned down to start kissing her again and she responded back, Annie realized she could get used to this. She was afraid to get used to Jeff and being together with him, when she assumed it was useless because he wouldn't want to keep it going. However, now that she knew that he wanted to, and even wanted to put in the work for it, it was a vast difference.

Now for the first time, Annie could feel safe to imagine doing this for a long time – maybe even longer than she could dare to dream right now. She could, but she realized there wasn't that much of a point to it.

There was little need to imagine or fear the future, because it would work itself out. It would because for maybe the first time since they met, Jeff and Annie were on the exact same page. They weren't hiding anything anymore, they both wanted the same things now, and they were each willing to fight for it and do it together. The rest would work itself out because of that.

And because of that, Annie finally felt safe enough to live in the moment.

A moment with a man who loved her, fought through years of doubt, self-loathing and excuses to be with her, made her feel safe and special, and let her know how safe and special she made him feel as well. The past and future remaining unresolved issues and relationship challenges didn't seem to matter as much compared to that. All that could be dealt with later because Annie knew that she and Jeff could defeat them now. Fully united, on the same page, and together.

After they finished this draining, mind blowing, hot, tight, warm and so _fucking good _sex, of course.

Once Jeff started using those fingers again, and Annie put her hands on his waist to finally get to those abs, she knew it wouldn't take much longer.

"Fucking…..please tell me you're close," Jeff got out. Annie smiled at his shaky voice, further emboldened by how little Annie was making sexual master Jeff Winger lose his composure the first time out. She hadn't even used those special tricks she found online over the years yet. But she could surprise him with those later – as now he deserved to just get off.

"Don't worry, I'm getting there….getting there…." Annie repeated while raising her hips to meet his thrusts. She then wrapped her arms back around him and made sure their naked chests were colliding and being pressed together. With that extra sensation of ample bare skin against ample bare skin, it was the final little trigger.

"Got there! Got there, oh God! Get there for me too, Jeff, fucking get it! Fuck me!" Annie yelled out with less coherency by the end.

With her going off for the second time, Jeff found one more burst of speed to get him over for the first time. Despite how he spilled into his condom and not into Annie, she was still swept by the most incredible sensations, as she felt him go off while she finished as well.

When they were both finished, Jeff fell on top of Annie, then took a lot of effort just to roll off and not crush her. Finally she was able to snuggle up with him and lay her head on his chest, trying not to feel too sappy about hearing his racing heart.

"You wanna review why that took three-and-a-half years again?" Jeff said with a limited amount of energy. "Actually, never mind. The first three years are kind of a drag, anyway."

"Good…..already sleepy,' Annie trailed off as their activities finally did a number on her. So did sleeping on Jeff for the first time and not beside him. She put a hand on his abs and stroked her thumb over them, as Jeff's exhausted and yet still sort of ragged breathing helped lull her back to sleep.

The next thing Annie knew, her head was still on Jeff's chest when she woke up, and she couldn't help but give it another few kisses. She wondered if this would wake Jeff up, then got her answer several moments later when she felt a hand go onto her cheek. Jeff then used that hand to pull her into kissing his lips, and Annie was briefly convinced she was still dreaming.

But there would be no need to dream about Jeff anyway – at least not any dreams that couldn't eventually become reality. Anything was possible now after sleeping together, having the hottest sex together, and both wanting it and more for longer than a fling. It was like something out of those movies on romcom night at…..

And with that, Annie remembered she was late to go home – then threw her clothes on when she saw _how_ late.

And with that, Annie couldn't get home in time before the whole apartment was totally wrecked, since Troy and Abed didn't have a script woman to keep their shoot in order.

And with that, Annie's nap on Jeff's chest was the last bit of real sleep she got for the next few days.

Worth. Three-Quarters. Of The Minutes.


End file.
